JPH0822865B2 - フェノール置換ジェム―ジホスホネート誘導体、その調製法およびそれを含む医薬組成物 - Google Patents

フェノール置換ジェム―ジホスホネート誘導体、その調製法およびそれを含む医薬組成物

Info

Publication number
JPH0822865B2
JPH0822865B2 JP1083855A JP8385589A JPH0822865B2 JP H0822865 B2 JPH0822865 B2 JP H0822865B2 JP 1083855 A JP1083855 A JP 1083855A JP 8385589 A JP8385589 A JP 8385589A JP H0822865 B2 JPH0822865 B2 JP H0822865B2
Authority
JP
Japan
Prior art keywords
diphosphonate
butyl
hydroxyphenyl
tetraethyl
tert
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
JP1083855A
Other languages
English (en)
Japanese (ja)
Other versions
JPH0222285A (ja
Inventor
ラン・ニュイアン
エリック・ニエゾール
ヒュー・ファン
ピエール・マエシュレール
クレイグ・ベンツエン
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SANFUAARU SA
Original Assignee
SANFUAARU SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by SANFUAARU SA filed Critical SANFUAARU SA
Publication of JPH0222285A publication Critical patent/JPH0222285A/ja
Publication of JPH0822865B2 publication Critical patent/JPH0822865B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/30Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839Polyphosphonic acids
    • C07F9/386Polyphosphonic acids containing hydroxy substituents in the hydrocarbon radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3839Polyphosphonic acids
    • C07F9/3865Polyphosphonic acids containing sulfur substituents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40Esters thereof
    • C07F9/4003Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4025Esters of poly(thio)phosphonic acids
    • C07F9/404Esters of poly(thio)phosphonic acids containing hydroxy substituents in the hydrocarbon radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40Esters thereof
    • C07F9/4003Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4025Esters of poly(thio)phosphonic acids
    • C07F9/4043Esters of poly(thio)phosphonic acids containing sulfur substituents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/38Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44Amides thereof
    • C07F9/4403Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4423Amides of poly (thio)phosphonic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • C07F9/65517Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657181Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Medicinal Chemistry (AREA)
  • Diabetes (AREA)
  • Engineering & Computer Science (AREA)
  • Obesity (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
JP1083855A 1988-03-31 1989-03-31 フェノール置換ジェム―ジホスホネート誘導体、その調製法およびそれを含む医薬組成物 Expired - Fee Related JPH0822865B2 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1239/88A CH675422A5 (he) 1988-03-31 1988-03-31
CH1239/88 1988-03-31

Publications (2)

Publication Number Publication Date
JPH0222285A JPH0222285A (ja) 1990-01-25
JPH0822865B2 true JPH0822865B2 (ja) 1996-03-06

Family

ID=4205733

Family Applications (1)

Application Number Title Priority Date Filing Date
JP1083855A Expired - Fee Related JPH0822865B2 (ja) 1988-03-31 1989-03-31 フェノール置換ジェム―ジホスホネート誘導体、その調製法およびそれを含む医薬組成物

Country Status (25)

Country Link
US (2) US5043330A (he)
EP (1) EP0339237B1 (he)
JP (1) JPH0822865B2 (he)
KR (1) KR0147830B1 (he)
CN (2) CN1024555C (he)
AR (1) AR247569A1 (he)
AT (1) ATE84040T1 (he)
AU (1) AU612475B2 (he)
CA (1) CA1338495C (he)
CH (1) CH675422A5 (he)
DE (2) DE339237T1 (he)
DK (1) DK173936B1 (he)
ES (1) ES2011210T3 (he)
FI (1) FI92933C (he)
GR (2) GR900300002T1 (he)
HU (1) HU203556B (he)
IE (1) IE62692B1 (he)
IL (1) IL89649A (he)
MY (1) MY103850A (he)
NO (1) NO891317L (he)
NZ (1) NZ228516A (he)
PH (1) PH27603A (he)
PT (1) PT90175B (he)
ZA (1) ZA892126B (he)
ZW (1) ZW3789A1 (he)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0377894A (ja) * 1989-08-18 1991-04-03 Toray Ind Inc メチレンジホスホン酸化合物
JPH05163150A (ja) * 1991-05-13 1993-06-29 E R Squibb & Sons Inc アテローム性動脈硬化症の抑制・治療剤
US5157027A (en) * 1991-05-13 1992-10-20 E. R. Squibb & Sons, Inc. Bisphosphonate squalene synthetase inhibitors and method
CA2067974A1 (en) * 1991-05-13 1992-11-14 Scott A. Biller Method for lowering cholesterol employing a phosphonomethylphosphinate squalene synthetase inhibitor
DK0594857T3 (da) * 1991-09-05 1998-10-07 Toray Industries Methandiphosphonsyrederivat, fremstilling deraf ogmedicinsk anvendelse deraf
EP0541037A3 (en) * 1991-11-06 1997-02-26 Takeda Chemical Industries Ltd Squalene synthetase inhibitory composition and use thereof
JPH06172372A (ja) * 1991-11-06 1994-06-21 Takeda Chem Ind Ltd スクアレン合成酵素阻害剤およびその用途
FR2683529B1 (fr) * 1991-11-12 1994-02-04 Bretagne Occidentale Universite Composes pharmaceutiques gem-diphosphonates analogues du cis-platine.
CH683996A5 (fr) * 1992-03-05 1994-06-30 Symphar Sa Dérivés aminophosphonates substitués, leur procédé de préparation et compositions pharmaceutiques les contenant.
DE69330114T2 (de) * 1992-07-10 2001-08-02 Toray Industries, Inc. Methandiphosphonat-derivat, dessen produktion und dessen verwendung als arzneimittel
US5332728A (en) * 1992-11-23 1994-07-26 Bristol-Myers Squibb Company Method for treating a fungal infection
US5434288A (en) * 1992-12-01 1995-07-18 Monsanto Company PLA2 inhibitors
ZA941088B (en) * 1993-02-19 1995-09-27 Symphar Sa Substituted ketophosphonates the processes for their preparation and pharmaceutical compositions containing them
AU674059B2 (en) * 1993-02-25 1996-12-05 Toray Industries, Inc. Process for producing methanediphosphonate compound
US5419845A (en) * 1994-03-15 1995-05-30 Basf Corporation Perfluorinated gemdiphosphonates as corrosion inhibitors for antifreeze coolants and other functional fluids
ATE235499T1 (de) * 1994-08-24 2003-04-15 Toray Industries Verfahren zur herstellung einer methanphosphonsäureverbindung
CH690163A5 (fr) * 1995-07-28 2000-05-31 Symphar Sa Dérivés gem-diphosphonates substitués utiles en tant qu'agents anti-cancers.
GB9603637D0 (en) * 1996-02-21 1996-04-17 Smithkline Beecham Plc Process
EP0952834A2 (en) * 1996-05-15 1999-11-03 The University of Sheffield Isopentenyl pyrophosphate isomerase (ipi) and/or prenyl transferase inhibitors
US6670398B2 (en) * 1997-05-14 2003-12-30 Atherogenics, Inc. Compounds and methods for treating transplant rejection
EA009987B1 (ru) * 1997-05-14 2008-04-28 Атеродженикс, Инк. Производные пробукола для лечения заболеваний, опосредованных vcam-1
US7008645B2 (en) 1998-07-14 2006-03-07 Yissum Research Development Company Of The Hebrew University Of Jerusalem Method of inhibiting restenosis using bisphosphonates
IL125336A0 (en) * 1998-07-14 1999-03-12 Yissum Res Dev Co Compositions for inhibition and treatment of restinosis
US6984400B2 (en) 1998-07-14 2006-01-10 Yissum Research Development Company Of The Hebrew University Of Jerusalem Method of treating restenosis using bisphosphonate nanoparticles
AUPQ872800A0 (en) * 2000-07-12 2000-08-03 Heart Research Institute, The Compositions and methods for treating cardiovascular disorders
GB0019272D0 (en) * 2000-08-04 2000-09-27 Symphar Sa Pharmaceutical compounds
WO2002087556A2 (en) * 2001-04-11 2002-11-07 Atherogenics, Inc. Probucol monoesters and their use to increase plasma hdl cholesterol levels and improve hdl functionality
EP1435970A4 (en) * 2001-10-18 2005-05-04 Ilex Products Inc METHOD OF TREATING SKIN WITH DIPHOSPHONATE DERIVATIVES
EP1485106A2 (en) * 2002-02-19 2004-12-15 Ilex Products, Inc. Phosphonate-phosphate and diphosphonate apolipoprotein e modulators
US20060205692A1 (en) * 2002-05-11 2006-09-14 Montes Imber F 1,1-and 1,2-Bisphosphonates as apoliprotein e modulators
WO2004064781A2 (en) * 2003-01-14 2004-08-05 Adam Heller Anti-inflammatory substituted phenols and elastomeric compositions for oral delivery of drugs
US10517883B2 (en) 2003-06-27 2019-12-31 Zuli Holdings Ltd. Method of treating acute myocardial infarction
CA2646334A1 (en) * 2006-03-17 2007-09-27 The Board Of Trustees Of The University Of Illinois Bisphosphonate compounds and methods
US8252840B2 (en) * 2007-03-26 2012-08-28 Salutria Pharmaceuticals Llc Methods of derivatives of probucol for the treatment of type II diabetes
US20080280985A1 (en) * 2007-03-27 2008-11-13 Scott Robert A D Methods and Compositions Using Certain Phenolic Derivatives for the Treatment of Diabetes
US9993427B2 (en) 2013-03-14 2018-06-12 Biorest Ltd. Liposome formulation and manufacture
EP3209671B8 (en) * 2014-10-21 2019-07-31 Council of Scientific and Industrial Research Alkylidene phosphonate esters as p-glycoprotein inducers
WO2018236221A2 (en) * 2017-06-03 2018-12-27 Can Holding B.V. DISSOLUTION OF NEURODEGENERATIVE PEPTIDE DEPOSITION

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA777769A (en) * 1963-03-18 1968-02-06 H. Roy Clarence Substituted methylene diphosphonic acid compounds and detergent compositions
DE1302557B (he) * 1963-04-09 1971-08-26
GB2043072B (en) * 1979-02-13 1983-11-23 Symphar Sa Diphosphonate compounds
US4416877A (en) * 1979-02-13 1983-11-22 Symphar S.A. Anti-atherosclerotic pharmaceutical compositions containing diphosphonate compounds
FR2531088B1 (fr) * 1982-07-29 1987-08-28 Sanofi Sa Produits anti-inflammatoires derives de l'acide methylenediphosphonique et leur procede de preparation
CH664158A5 (fr) * 1984-07-18 1988-02-15 Symphar Sa Derives propylidenediphosphonates-1,3 substitues en position 2, leur procede de preparation et compositions pharmaceutiques les contenant.
US6259935B1 (en) * 1997-06-24 2001-07-10 Matsushita Electrical Industrial Co., Ltd. Electro-mechanical-acoustic transducing device

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TETRAHEDRON,vol.30,p.301〜305(1974)

Also Published As

Publication number Publication date
DK148189A (da) 1989-10-17
ZA892126B (en) 1989-11-29
NO891317D0 (no) 1989-03-29
AR247569A1 (es) 1995-01-31
EP0339237A3 (en) 1991-01-09
ES2011210T3 (es) 1994-01-01
MY103850A (en) 1993-09-30
IE62692B1 (en) 1995-02-22
DE68904104T2 (de) 1993-06-17
AU3224389A (en) 1989-10-05
AU612475B2 (en) 1991-07-11
NO891317L (no) 1989-10-02
GR900300002T1 (en) 1991-06-07
FI891538A (fi) 1989-10-01
IE890802L (en) 1989-09-30
ZW3789A1 (en) 1989-08-23
US5043330A (en) 1991-08-27
KR0147830B1 (ko) 1998-08-17
PT90175A (pt) 1989-11-10
HUT50482A (en) 1990-02-28
PT90175B (pt) 1994-06-30
HU203556B (en) 1991-08-28
IL89649A0 (en) 1989-09-28
IL89649A (he) 1995-07-31
FI92933C (fi) 1995-01-25
NZ228516A (en) 1990-12-21
FI92933B (fi) 1994-10-14
DK173936B1 (da) 2002-02-25
CN1086820A (zh) 1994-05-18
KR890014569A (ko) 1989-10-24
DE68904104D1 (de) 1993-02-11
US5128331A (en) 1992-07-07
GR3007442T3 (he) 1993-07-30
ES2011210A4 (es) 1990-01-01
CN1036772A (zh) 1989-11-01
CH675422A5 (he) 1990-09-28
DK148189D0 (da) 1989-03-28
FI891538A0 (fi) 1989-03-30
CA1338495C (en) 1996-07-30
EP0339237B1 (en) 1992-12-30
JPH0222285A (ja) 1990-01-25
DE339237T1 (de) 1990-02-08
ATE84040T1 (de) 1993-01-15
CN1024555C (zh) 1994-05-18
EP0339237A2 (en) 1989-11-02
PH27603A (en) 1993-08-31

Similar Documents

Publication Publication Date Title
JPH0822865B2 (ja) フェノール置換ジェム―ジホスホネート誘導体、その調製法およびそれを含む医薬組成物
US5091378A (en) Phosphorus-containing HMG-CoA reductase inhibitors, new intermediates and method
EP0559079B1 (en) Substituted aminophosphonate derivatives, process for their preparation and pharmaceutical compositions containing them
AU663268B2 (en) Novel methylenebisphosphonic acid derivatives
FI87927C (fi) Foerfarande foer framstaellining av nya fosforhaltiga hmg-coa-reduktasinhibitorer och nya mellanprodukter
JP2929236B2 (ja) カルシウム代謝異常による疾病用治療剤
AU657554B2 (en) Dialkyl (dialkoxyphosphinyl)methyl phosphates as anti-inflammatory agents
JPH07506121A (ja) 置換ホスホネート,その製法およびその化合物含有の医薬組成物
US5212164A (en) Phosphorus-containing squalene synthetase inhibitors
US4853476A (en) Phosphorus containing compounds as inhibitors of enkephalinases
KR20010031269A (ko) 신규한 메틸렌비스포스폰산 유도체
GB2079285A (en) Diphosphonate derivatives and pharmaceutical compositions containing them
US5273969A (en) Phosphorus-containing squalene synthetase inhibitors and method
US5107011A (en) Isoprenoid phosphinylformic acid squalene synthetase inhibitors and method
US5166386A (en) Process of making isoprenoid phosphinylformic acid squalene synthetase inhibitors
JPH04275265A (ja) α−アミノ酸誘導体
WO2004026242A2 (en) Substituted ketophosphonate inhibitors of tumor cell proliferation

Legal Events

Date Code Title Description
R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees